300psi is not very low, its actually the minimum compression listed by GM for the LB7 in the manual. The fact you have no variation across the cylinders is what is most important.
I don't know where the Duramax usually tests for cylinder leakage, as it is generally a very tight engine in my experiences, but in general the rule of thumb I've always heard is 10-20% being normal for a good street engine as long as you don't notice a lot of air escaping out of exhaust, intake etc.
How did the compression buildup when doing the compression test? If the rings are leaking it should be slow to buildup, but should still hit the peak pressure (300psi in your case). If the valves are leaking it should be very slow and not hit the peak, don't confuse this with a bent rod which will often build pressure fast like it should, just with a low peak pressure. Low meaning lower than the average of the other cylinders. I suspect a cracked piston would act like a leaking valve building pressure slowly and not hitting a peak. Not a common issue with the LB7 pistons though.